Bromotrimethylsilane
TMSBR · TRIMETHYLSILYL BROMIDE · TRIMETHYLBROMOSILANE · TMBS · (CH3)3SiBr · Silane, bromotrimethyl- · Trimethylsilicon bromide · CT2928
Identifiers & Physical Properties
| CAS No. | 2857-97-8 |
|---|---|
| Molecular formula | C3H9BrSi |
| Average molar mass | 153.09 g/mol |
| Monoisotopic mass | 151.96568892 g/mol |
| SMILES | C[Si](C)(C)Br |
| InChIKey | IYYIVELXUANFED-UHFFFAOYSA-N |
| PubChem CID | 76113 |
| EC No. | 220-672-0 |
| DTXSID | DTXSID1062671 |
Chemical & Physical Properties
| Topological polar surface area | 0 |
|---|---|
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 0 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 28.4 |
| SpringerMaterials Properties | 29Si nuclear magnetic resonance spectrum |
| Density | 1.16 @25 °C1.16 g/mL at 25 °C(lit.) |
| Boiling point | 79 °C @760 [mm Hg]79 °C(lit.) |
| Melting point | -43 °C |
| Refractive index | n20/D 1.424(lit.) |
| Flash point | 90 °F |
| Storage conditions | Store below +30°C. |
| Solubility | DECOMPOSES |
| Physical state | Liquid |
| Specific gravity | 1.1725 |
| Color | Clear colorless to yellow |
| Sensitivity | Moisture Sensitive |
| Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
| BRN | 1731135 |
| Stability | Stable. Flammable. Incompatible with strong acids, strong oxidizing agents. May decompose on exposure to water or moist air. |
| InChI | 1S/C3H9BrSi/c1-5(2,3)4/h1-3H3 |
| InChIKey | IYYIVELXUANFED-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)Br |
| CAS DataBase Reference | 2857-97-8(CAS DataBase Reference) |
| FDA UNII | JHH5G299BX |
| NIST Chemistry Reference | Bromotrimethylsilane(2857-97-8) |
| EPA Substance Registry System | Silane, bromotrimethyl- (2857-97-8) |
| UNSPSC Code | 12352103 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS05,GHS07,GHS09 |
| Signal word | Danger |
| GHS hazard statements | H225-H314-H335-H410 |
| GHS precautionary statements | P210-P233-P273-P280-P303+P361+P353-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | C |
| Risk statements (R) | 10-34-29-14 |
| Safety statements (S) | 16-26-36/37/39-45-8 |
| UN transport number | UN 2920 8/PG 2 |
| Water hazard class (WGK) | 3 |
| F | 10-21 |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSTOT SE 3 |
| Packing group | II |
| Customs code | 29310095 |
| Storage class | 3 - Flammable liquids |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH225 (15.1%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 53 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24353Bromotrimethylsilane: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Flam. Liq. 2 (15.1%) |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| F | 10-21 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 2920 8/PG 2 |
| Customs code | 29310095 |
| Risk statements (R) | 10-34-29-14 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05,GHS07,GHS09 |
| Hazard symbols | C |
| Safety statements (S) | 16-26-36/37/39-45-8 |
| Hazard class | 3Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSTOT SE 3 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| Target organs | Respiratory system |
| GHS hazard statements | H225-H314-H335-H410 |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| GHS precautionary statements | P210-P233-P273-P280-P303+P361+P353-P305+P351+P338 |
Applications & Uses
Uses
Bromotrimethylsilane can protect or deprotect functional groups selectively, act as silane blocking agent, which is widely used in the syntheses of drugs.
Uses
Adefovir intermediate
Uses
Powerful silylating agent
Uses
Bromotrimethylsilane is a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers; effective reagent for formation of silyl enol ethers; can function as brominating agent.Amines react with TMS-Br to form isolable adducts, which react readily with ketones to form enamines under mild conditions (eq 15).
General Description
Bromotrimethylsilane is used with Cl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.
Preparation & Synthesis
Preparation
although many methods are reported, only a few are provided here: chlorotrimethylsilane undergoes halogen exchange with either magnesium bromide in Et2O or sodium bromide in MeCN, which allows in situ reagent formation (eq 1); alternatively, hexamethyldisilane reacts with bromine in benzene solution or neat, to afford only TMS-Br with no byproducts (eq 2).4 TMS-Br may also be generated by reaction of hexamethyldisiloxane and aluminum bromide (eq 3).However, it should be noted that the reactivity of in situ generated reagent appears to depend upon the method of preparation.